(Z)-N-{3-[(6-Chloro­pyridin-3-yl)meth­yl]-1,3-thia­zolidin-2-yl­idene}cyanamide

Gao, J.-S.; Qiao, J.; Yu, Y.-H.; Hou, G.-F.

doi:10.1107/S1600536811013316

Volume 67
Part 5
Page o1140
May 2011

Received 2 April 2011
Accepted 8 April 2011
Online 16 April 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.048
wR = 0.137
Data-to-parameter ratio = 17.8
Details

(Z)-N-{3-[(6-Chloropyridin-3-yl)methyl]-1,3-thiazolidin-2-ylidene}cyanamide

Jin-Sheng Gao,^a,^b ^* Jun Qiao,^a Ying-Hui Yu ^a and Guang-Feng Hou ^b

^aCollege of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China, and ^bEngineering Research Center of Pesticide of Heilongjiang Province, Heilongjiang University, Harbin 150080, People's Republic of China
Correspondence e-mail: hgf1000@163.com

The asymmetric unit of the title compound, C₁₀H₉ClN₄S, common name thiacloprid, comprises two molecules. In both molecules, the thiazolidine rings are almost planar (with r.m.s. deviations of 0.016 and 0.065 Å) and form dihedral angles of 73.36 (6) and 70.25 (8)° with the 2-chloropyridine rings. In the crystal, intermolecular C-HN hydrogen bonds links the molecules into chains propagating in [ $[\overline1]$ 01].

Related literature

For background to the title compound, a member of the neonicotinoide class of insecticides, see Maienfisch et al. (2003). For the synthesis, see Ishimitsu et al., (1991)

Experimental

Crystal data

C₁₀H₉ClN₄S
M_r = 252.73
Monoclinic, P 2₁ /c
a = 7.1294 (14) Å
b = 35.469 (7) Å
c = 9.0211 (18) Å
= 97.80 (3)°
V = 2260.1 (8) Å³
Z = 8
Mo K radiation
= 0.50 mm^-1
T = 293 K
0.31 × 0.29 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) T_min = 0.863, T_max = 0.909
21869 measured reflections
5151 independent reflections
3505 reflections with I > 2(I)
R_int = 0.046

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.137
S = 1.08
5151 reflections
289 parameters
H-atom parameters constrained
_max = 0.21 e Å^-3
_min = -0.29 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C3-H3N5ⁱ	0.93	2.55	3.459 (4)	167
C13-H13N1ⁱⁱ	0.93	2.49	3.408 (4)	169
Symmetry codes: (i) x-1, y, z; (ii) x, y, z+1.

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KP2319 ).

Acknowledgements

The authors thank the Special Funds for the Research of Scientific and Technological Innovative Talents of Harbin Municipal Science and Technology Bureau (2009RFXXG027), the Science and Technology Planning Project of Heilongjiang Province (GZ08A401) and Heilongjiang University for supporting this study.

References

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Ishimitsu, K., Suzuki, J., Ohishi, H., Yamada, T., Hatano, R., Takakusa, N. & Mitsui, J. (1991). WO Patent 91/04965.
Maienfisch, P., Haettenschwiler, J., Rindlisbacher, A., Decock, A., Wellmann, H. & Kayser, H. (2003). Chimia, 57, 710-714.
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds